Beckmann rearrangement of 15N-cyclohexanone oxime on zeolites silicalite-1, H-ZSM-5, and H-[B]ZSM-5 studied by solid-state NMR spectroscopy

V. R Reddy Marthala, Yijiao Jiang, Jun Huang, Wei Wang*, Roger Gläser, Michael Hunger

*Corresponding author for this work

Research output: Contribution to journalArticle

59 Citations (Scopus)

Abstract

By means of solid-state 15N NMR spectroscopy, evidence for the formation of nitrilium ions as intermediates of the Beckmann rearrangement of 15N-cyclohexanone oxime to ε-caprolactam on silicalite-1, H-ZSM-5, and H-[B]ZSM-5 is reported. The zeolites under study are characterized by different acid strengths (silicalite-1 < H-[B]ZSM-5 < H-ZSM-5). Depending on the nature of catalytically active surface OH groups, reactant and product molecules exist in the nonprotonated or protonated state. In addition, formation of byproducts such as 5-cyano-1-pentene and ε-aminocapric acid as a result of dehydration and hydrolysis of the reactant and product molecules, respectively, were observed.

Original languageEnglish
Pages (from-to)14812-14813
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number46
DOIs
Publication statusPublished - 22 Nov 2006
Externally publishedYes

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